CO4980875A1 - NEW DERIVATIVES OF ECHINOCANDINE, ITS PREPARATION PROCEDURE AND ITS APPLICATION AS FUNGICIDES - Google Patents
NEW DERIVATIVES OF ECHINOCANDINE, ITS PREPARATION PROCEDURE AND ITS APPLICATION AS FUNGICIDESInfo
- Publication number
- CO4980875A1 CO4980875A1 CO98073452A CO98073452A CO4980875A1 CO 4980875 A1 CO4980875 A1 CO 4980875A1 CO 98073452 A CO98073452 A CO 98073452A CO 98073452 A CO98073452 A CO 98073452A CO 4980875 A1 CO4980875 A1 CO 4980875A1
- Authority
- CO
- Colombia
- Prior art keywords
- radical
- hydrogen atom
- formula
- carbon atoms
- heteroatoms
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 11
- 125000004432 carbon atom Chemical group C* 0.000 abstract 10
- -1 hydroxide radical Chemical class 0.000 abstract 10
- 150000003254 radicals Chemical class 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000005842 heteroatom Chemical group 0.000 abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 6
- 125000005843 halogen group Chemical group 0.000 abstract 4
- 125000004122 cyclic group Chemical group 0.000 abstract 3
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- WUPSJTQKGFMDON-UHFFFAOYSA-N Mulundocandin Natural products N1C(=O)C2CC(O)CN2C(=O)C(C(C)O)NC(=O)C(NC(=O)CCCCCCCCCCC(C)CC)CC(O)C(O)NC(=O)C2C(O)C(C)CN2C(=O)C(CO)NC(=O)C1C(O)C(O)C1=CC=C(O)C=C1 WUPSJTQKGFMDON-UHFFFAOYSA-N 0.000 abstract 1
- WUPSJTQKGFMDON-FUMJLYDLSA-N N-[(3S,6S,9S,11R,15S,18S,20R,21R,24S,25S,26S)-6-[(1S)-1,2-dihydroxy-2-(4-hydroxyphenyl)ethyl]-11,20,21,25-tetrahydroxy-15-[(1R)-1-hydroxyethyl]-3-(hydroxymethyl)-26-methyl-2,5,8,14,17,23-hexaoxo-1,4,7,13,16,22-hexazatricyclo[22.3.0.09,13]heptacosan-18-yl]-12-methyltetradecanamide Chemical compound CCC(C)CCCCCCCCCCC(=O)N[C@H]1C[C@@H](O)[C@@H](O)NC(=O)[C@@H]2[C@@H](O)[C@@H](C)CN2C(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H]2C[C@@H](O)CN2C(=O)[C@@H](NC1=O)[C@@H](C)O)[C@H](O)C(O)c1ccc(O)cc1 WUPSJTQKGFMDON-FUMJLYDLSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 108010084578 mulundocandin Proteins 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/18—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
En todas las formas de isómeros posibles, así como susmezclas, los compuestos de fórmula (I)En los cuales o bien R1 y R2, idénticos o diferentes uno de otro, representan un átomo de hidrógeno, un radical hidróxido, un radical alquilo que contiene hasta 8 átomos de carbono, lineal, ramificado o cíclico, eventualmente interrumpido por un átomo de oxígeno eventualmente sustituido con un átomo de halógeno, un radical CH, un radical representado a y b un átomo de hidrógeno o un radical alquilo que contiene hasta 8 átomos de carbono, pudiendo a y b eventualmente formar con el átomo de nitrógeno un heterociclo , que contiene eventualmente uno o varios heteroátomos suplementarios, o bien NR1 forma con el átomo de carbono endocíclico que lleva el radical , un doble enlace y o bien R2representa un radical XRa , representando X un átomo de oxígeno o un radical NH, o N-alquilo que contiene hasta 8 átomos de carbono, y Ra representa un átomo de hidrógeno, un radical alquilo lineal ramificado o cíclico, que contiene hasta 8 átomos de carbono, eventualmente sustituido con uno o varios átomos de halógeno, con uno o varios radicales CH, - 2 -CO2 H, CO2 alc, con un radical , representado a´ y b´un átomo de hidrógeno, un radical alquilo que contiene hasta 8 átomos de carbono, pudiendo a´ y b´ formar un heterociclo que contiene eventualmente uno o varios heteroátomos suplementarios y/o con un heterociclo que contiene uno o varios heteroátomos suplementarios y/o con un heterociclo que contiene uno o varios heteroátomos , o representado R2 un radicalen el que d, e, f y g representan cada uno un átomo de hidrógeno o un radical alquilo que contiene hasta 8 átomos de carbono , pudiendo f y g además representar un radical acilo que contiene hasta 8 átomos de carbono, pudiendo e y f igualmente formar un anillo que contiene eventualmente uno o varios heteroátomos,R3 representa un átomo de hidrógeno, un radical metilo o hidróxilo , R4 representa un átomo de hidrógeno o un radical hidróxilo, R representa una cadena lineal, ramificada o cíclica, que contiene hasta 30 átomos de carbono, la cual contiene eventualmente uno o varios heteroátomos, uno o varios heterociclos, o un radical acilo lineal, ramificado o cíclico, que contiene hasta 30 átomos de carbono, el cual contiene eventualmente uno o varios heteroátomos y/o uno o varios heterociclos, T representa un átomo de hidrógeno, un radical metilo, un radical CH2 CONH2 , CH2 C=N, un radical (CH2 )2 NH2 o (CH2 )2 Nalc+ X-, siendo X un átomo de halógeno y alc un radical de alquilo que contiene hasta 8 átomos de carbono,Y representa un átomo de hidrógeno, un radical hidróxilo o un átomo de halógeno, o un radical OSO3 H o una de las sales de este radicalW representa un átomo de hidrógeno o un radical CH, Z representa un átomo de hidrógeno o un radical metilo, así como las sales por adición con ácidos de los productos de fórmula (I).Nuevos compuestos de la fórmula (II),cuyos sustituyentes están definidos en la reivindicación 1, útiles para obtener los compuestos de fórmula 1. de la reivindicación 1.Nuevos compuestos de la fórmula (III)cuyos sustituyentes están definidos en la reivindicación 1, compuestos intermedios para la obtención del compuesto de la fórmula (II) de acuerdo con la reivindicación 20.Nuevos compuestos de la fórmula (IV)donde R conserva su significado de precedente, útiles para la obtención del compuesto de la fórmula (II) de la reivindicación 20, con excepción de mulundocandina y deoximulundocandina.las composiciones farmacéuticas que contienen en calidad de medicamento al menos un compuesto de fórmula (I) definida en un cualquiera de las reivindicaciones 1 a 18, así como sus sales por adición con ácidos farmacéuticamente aceptables.In all possible forms of isomers, as well as their mixtures, the compounds of formula (I) in which either R1 and R2, identical or different from each other, represent a hydrogen atom, a hydroxide radical, an alkyl radical containing up to 8 carbon atoms, linear, branched or cyclic, optionally interrupted by an oxygen atom optionally substituted by a halogen atom, a CH radical, a radical represented a and b by a hydrogen atom or an alkyl radical containing up to 8 carbon atoms where a and b may optionally form with the nitrogen atom a heterocycle, possibly containing one or more additional heteroatoms, or NR1 forms with the endocyclic carbon atom bearing the radical, a double bond and either R2 represents a radical XRa, X representing a oxygen atom or an NH, or N-alkyl radical containing up to 8 carbon atoms, and Ra represents a hydrogen atom, an alkyl radical or linear branched or cyclic, containing up to 8 carbon atoms, optionally substituted with one or more halogen atoms, with one or more radicals CH, - 2 -CO2 H, CO2 alc, with one radical, represented a´ and b´un hydrogen atom, an alkyl radical containing up to 8 carbon atoms, a´ and b´ being able to form a heterocycle possibly containing one or more supplementary heteroatoms and / or with a heterocycle containing one or more supplementary heteroatoms and / or with a heterocycle containing one or more heteroatoms, or represented by R2 a radical in which d, e, f and g each represent a hydrogen atom or an alkyl radical containing up to 8 carbon atoms, and f and g may also represent an acyl radical containing up to 8 atoms of carbon, since e and f may also form a ring possibly containing one or more heteroatoms, R3 represents a hydrogen atom, a methyl or hydroxyl radical, R4 represents a hydrogen atom or a hydroxyl radical, R represents a linear, branched or cyclic chain, containing up to 30 carbon atoms, which eventually contains one or more heteroatoms, one or more heterocycles, or a linear, branched or cyclic acyl radical , containing up to 30 carbon atoms, which optionally contains one or more heteroatoms and / or one or more heterocycles, T represents a hydrogen atom, a methyl radical, a CH2 CONH2 radical, CH2 C = N, a radical (CH2 ) 2 NH2 or (CH2) 2 Nalc + X-, where X is a halogen atom and alc is an alkyl radical containing up to 8 carbon atoms, Y represents a hydrogen atom, a hydroxyl radical or a halogen atom, or a radical OSO3 H or one of the salts of this radicalW represents a hydrogen atom or a CH radical, Z represents a hydrogen atom or a methyl radical, as well as the acid addition salts of the products of formula (I). compounds of the f formula (II), whose substituents are defined in claim 1, useful for obtaining the compounds of formula 1. of claim 1. New compounds of formula (III) whose substituents are defined in claim 1, intermediate compounds for obtaining of the compound of formula (II) according to claim 20. New compounds of formula (IV) where R retains its precedent meaning, useful for obtaining the compound of formula (II) of claim 20, except of mulundocandin and deoximulundocandin. Pharmaceutical compositions containing as medicament at least one compound of formula (I) defined in any one of claims 1 to 18, as well as their addition salts with pharmaceutically acceptable acids.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9715628A FR2772028B1 (en) | 1997-12-10 | 1997-12-10 | NOVEL ECHINOCANDIN DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS FUNGICIDES |
| FR9813361A FR2784993B1 (en) | 1998-10-26 | 1998-10-26 | NOVEL ECHINOCANDIN DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS FUNGICIDES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CO4980875A1 true CO4980875A1 (en) | 2000-11-27 |
Family
ID=26233984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CO98073452A CO4980875A1 (en) | 1997-12-10 | 1998-12-10 | NEW DERIVATIVES OF ECHINOCANDINE, ITS PREPARATION PROCEDURE AND ITS APPLICATION AS FUNGICIDES |
Country Status (43)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA72200C2 (en) * | 1997-12-10 | 2005-02-15 | Авентіс Фарма С.А. | Echinocandine derivatives, a method for producing the same and use thereof as antifungal agents |
| WO2000024694A1 (en) * | 1998-10-28 | 2000-05-04 | Eli Lilly And Company | Photochemical process for making 1-deoxy-2-keto derivatives |
| FR2794747B1 (en) | 1999-06-09 | 2004-04-16 | Hoechst Marion Roussel Inc | NOVEL ECHINOCANDIN DERIVATIVES, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS ANTI-FUNGI |
| FR2794746B1 (en) * | 1999-06-09 | 2002-12-06 | Hoechst Marion Roussel Inc | NOVEL ECHINOCANDIN DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS ANTI-FUNGAL |
| FR2833596B1 (en) * | 2001-12-14 | 2005-02-18 | Aventis Pharma Sa | PROCESS FOR THE PREPARATION OF ECHINOCANDIN DERIVATIVES |
| CN101659693B (en) * | 2008-08-27 | 2012-11-21 | 上海医药工业研究院 | Method for preparing pneumocandin B0 |
| CN101659692B (en) * | 2008-08-27 | 2012-07-04 | 上海医药工业研究院 | Method for preparing echinocandin B |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2241955A (en) * | 1990-03-16 | 1991-09-18 | Merck & Co Inc | Cyclohexapeptide compounds |
| TW264477B (en) * | 1992-03-19 | 1995-12-01 | Lilly Co Eli | |
| US5516757A (en) * | 1994-09-16 | 1996-05-14 | Merck & Co., Inc. | Semi-synthetic lipopeptides, compositions containing said lipopeptides, and methods of use |
| US5516756A (en) | 1994-10-31 | 1996-05-14 | Merck & Co., Inc. | Aza cyclohexapeptide compounds |
| WO1996022784A1 (en) * | 1995-01-26 | 1996-08-01 | Merck & Co., Inc. | Novel antifungal cyclohexapeptides |
| US5646111A (en) * | 1995-04-07 | 1997-07-08 | Eli Lilly And Company | Cyclic peptide antifungal Agents |
| UA72200C2 (en) * | 1997-12-10 | 2005-02-15 | Авентіс Фарма С.А. | Echinocandine derivatives, a method for producing the same and use thereof as antifungal agents |
| FR2794747B1 (en) * | 1999-06-09 | 2004-04-16 | Hoechst Marion Roussel Inc | NOVEL ECHINOCANDIN DERIVATIVES, PROCESS FOR PREPARING THEM AND THEIR APPLICATION AS ANTI-FUNGI |
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1998
- 1998-09-12 UA UA2000074030A patent/UA72200C2/en unknown
- 1998-12-08 TN TNTNSN98222A patent/TNSN98222A1/en unknown
- 1998-12-09 MA MA25378A patent/MA26575A1/en unknown
- 1998-12-09 EE EEP200000336A patent/EE04837B1/en not_active IP Right Cessation
- 1998-12-09 EA EA200000625A patent/EA002706B1/en not_active IP Right Cessation
- 1998-12-09 SK SK839-2000A patent/SK286916B6/en not_active IP Right Cessation
- 1998-12-09 CA CA002311295A patent/CA2311295A1/en not_active Abandoned
- 1998-12-09 NZ NZ504614A patent/NZ504614A/en unknown
- 1998-12-09 TR TR2000/01655T patent/TR200001655T2/en unknown
- 1998-12-09 AT AT98959935T patent/ATE321772T1/en active
- 1998-12-09 PA PA19988464201A patent/PA8464201A1/en unknown
- 1998-12-09 IL IL13664798A patent/IL136647A0/en active IP Right Grant
- 1998-12-09 DK DK98959935T patent/DK1036090T3/en active
- 1998-12-09 PT PT98959935T patent/PT1036090E/en unknown
- 1998-12-09 BR BR9813531-7A patent/BR9813531A/en not_active IP Right Cessation
- 1998-12-09 RS YUP-339/00A patent/RS49905B/en unknown
- 1998-12-09 JP JP2000524307A patent/JP4361679B2/en not_active Expired - Fee Related
- 1998-12-09 PL PL341012A patent/PL196889B1/en not_active IP Right Cessation
- 1998-12-09 DZ DZ980280A patent/DZ2670A1/en active
- 1998-12-09 AU AU15659/99A patent/AU755033B2/en not_active Ceased
- 1998-12-09 AP APAP/P/2000/001826A patent/AP1260A/en active
- 1998-12-09 UY UY25292A patent/UY25292A1/en not_active IP Right Cessation
- 1998-12-09 CZ CZ20002113A patent/CZ301919B6/en not_active IP Right Cessation
- 1998-12-09 OA OA00000164A patent/OA11899A/en unknown
- 1998-12-09 GE GEAP19985441A patent/GEP20032975B/en unknown
- 1998-12-09 CN CN98813413A patent/CN1284084A/en active Pending
- 1998-12-09 EP EP98959935A patent/EP1036090B1/en not_active Expired - Lifetime
- 1998-12-09 HU HU0100263A patent/HUP0100263A3/en unknown
- 1998-12-09 WO PCT/FR1998/002671 patent/WO1999029716A1/en active Application Filing
- 1998-12-09 DE DE69834057T patent/DE69834057T2/en not_active Expired - Lifetime
- 1998-12-09 US US09/581,451 patent/US6677429B1/en not_active Expired - Fee Related
- 1998-12-09 ES ES98959935T patent/ES2259462T3/en not_active Expired - Lifetime
- 1998-12-09 KR KR1020007006268A patent/KR100564872B1/en not_active IP Right Cessation
- 1998-12-09 AP APAP/P/2003/002874A patent/AP1567A/en active
- 1998-12-10 PE PE1998001202A patent/PE130099A1/en not_active Application Discontinuation
- 1998-12-10 CO CO98073452A patent/CO4980875A1/en unknown
- 1998-12-10 AR ARP980106281A patent/AR016432A1/en active IP Right Grant
-
1999
- 1999-01-22 TW TW087121185A patent/TW446541B/en not_active IP Right Cessation
- 1999-04-05 SA SA99191248A patent/SA99191248B1/en unknown
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2000
- 2000-05-31 BG BG104494A patent/BG65033B1/en unknown
- 2000-06-07 CU CU20000136A patent/CU22962A3/en unknown
- 2000-06-08 IL IL136647A patent/IL136647A/en not_active IP Right Cessation
- 2000-06-09 HR HR20000384A patent/HRP20000384B1/en not_active IP Right Cessation
- 2000-06-09 NO NO20002959A patent/NO327498B1/en not_active IP Right Cessation
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2003
- 2003-09-19 US US10/666,072 patent/US7160983B2/en not_active Expired - Fee Related
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2005
- 2005-06-23 US US11/165,458 patent/US7285619B2/en not_active Expired - Fee Related
- 2005-12-06 IL IL172412A patent/IL172412A/en not_active IP Right Cessation
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2006
- 2006-05-30 CY CY20061100686T patent/CY1105695T1/en unknown
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2007
- 2007-06-24 IL IL184171A patent/IL184171A0/en unknown
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